A major talking point tof moving to Qubes was to avoid this problem. When I connect sys-whonix to Tor I get a message in the message box that says "Connecting to Tor" and then "Connect to Tor". There is simply no reason on earth why that message cannot also read, when necessary, "A new distribution to Whonix is now available. Please see the whonix website for special instructions."
These messages are the exact reason why people like myself do not run Whonix Check on a regular basis. There is no need because we get those notifications another way.
There is a way to deliver the correct information to the user right at the desktop. It's not being used. Instead, what we have is notifications cast to the wind and pray that the user sees one of them and if not, well, their bad luck.